In this page, we're going to discuss another product that forms when carbonyls react with alcohols, and that's called acetals. In general, I'm just going to say a few facts, and then we're going to go straight into the mechanism. The first fact I want you to know is that acetals, once formed, are actually stable in base. If you want to keep an acetal for a long time, keep it in a neutral to basic solution. However, they're easily hydrolyzed back to carbonyls using acid. That makes sense, guys, because remember that this is a reversible reaction. It's acid catalyzed. It makes sense that if you use acid, you're going to go back to the carbonyl and it's going to be in equilibrium. If you want to specifically make an acetal that not only has ROR but is actually cyclic, meaning it forms a ring, then you're going to have to use a diol because a diol is going to have carbons in the middle that are going to link together. For example, the diol that I would need here would be 1,2-ethanediol
21. Aldehydes and Ketones: Nucleophilic Addition
Acetal
21. Aldehydes and Ketones: Nucleophilic Addition
Acetal - Video Tutorials & Practice Problems
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General Mechanism
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ProblemProvide the chemical steps necessary for the following synthesis.
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ProblemProvide the chemical steps necessary for the following synthesis.
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ProblemDetermine the starting materials based on the acetal group present.
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PRACTICE PROBLEMS AND ACTIVITIES (18)
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- Which of the following are a. hemiacetals? b. acetals? c. hydrates? 1. (CH3)2COCH3(OH)
- Which of the following are a. hemiacetals? b. acetals? c. hydrates? 3. (OCH3)2CH3CH
- Identify A through O: